Synthesis of Trifunctional Thiazole-Fused Anthranilonitrile and Anthranilic Acid Derivatives

The synthesis of trifunctional isomeric benzothiazoles derived from nitroanthranilic acids and their corresponding anthranilonitrile analogues is studied. Compared to previous work, the reaction sequence affords convenient access to hitherto undescribed 2-cyanobenzothiazoles. For further synthetic applications of these poly-functional compounds, a hydrolysis-decarboxylation sequence is per -formed in an acidic medium (HCl or HBr), leading to an enlarged array of relevant building blocks.

Automated summary

The synthesis of trifunctional isomeric benzothiazoles derived from nitroanthranilic acids and their corresponding anthranilonitrile analogues is studied, providing a convenient access to previously unreported 2-cyanobenzothiazoles. A hydrolysis-decarboxylation sequence is then performed in an acidic medium to expand the range of relevant building blocks for further synthetic applications of these poly-functional compounds.